Abstract
An anti-candidiasis glycoconjugate vaccine was prepared via a tyrosine-selective alkynylation and a click chemistry mediated glycoconjugation sequence. It features a well-defined glycan, protein carrier, and connectivity. The construct, although with significantly lower carbohydrate loading and a shorter β-(1,3) glucan chain than the well-established anti-candidiasis vaccine derived from the random conjugation of laminarin at lysines, elicited a comparable level of specific IgG antibodies.
Highlights
Glycoconjugate vaccines derived from the covalent coupling of microbial poly- or oligosaccharides to a protein carrier are crucial for the prevention of many lifethreatening infectious diseases.[5,6,7]
The glycan antigen and protein carrier and the connectivity may be crucial to the immunogenicity of the carbohydrate-based conjugate vaccines, and is a key aspect of the structure–activity relationships (SARs).[14,15]
We envisaged that a well-de ned alkynyl-protein carrier with broad applicability would be essential to a general strategy, given the fact that various structurally-de ned glycans can be obtained by total synthesis.[8,9,10,11,12]
Summary
Bioconjugation is of great importance to biotherapies and chemical biology.[1,2,3,4] Glycoconjugate vaccines derived from the covalent coupling of microbial poly- or oligosaccharides to a protein carrier are crucial for the prevention of many lifethreatening infectious diseases.[5,6,7] To date, all licensed conjugate vaccines are still prepared and used as complex mixtures. Well-de ned constructs are highly desirable to ensure consistent and optimal efficacy, and to facilitate studies of immunological mechanisms. Signi cant efforts have been applied to the development of chemical and enzymatic methods for the synthesis of structurally well-de ned carbohydrates with high purity.[8,9,10,11,12] the conjugation steps for almost all licensed vaccines employ the surface abundant lysines as the attachment points. The glycan antigen and protein carrier and the connectivity may be crucial to the immunogenicity of the carbohydrate-based conjugate vaccines, and is a key aspect of the structure–activity relationships (SARs).[14,15] we present a general strategy to a well-de ned glycoconjugate vaccine against Candida albicans through tyrosine-selective conjugation
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